


Mr. Winchester's Little Boy

by orphan_account



Category: Supernatural
Genre: Age Regression/De-Aging, Angst, Cursed Dean, Daddy Sam, De-Aged Dean Winchester, F/M, Fluff, Little Dean, Little Dean Winchester - Freeform, POV Original Female Character
Language: English
Status: In-Progress
Published: 2017-09-26
Updated: 2017-11-30
Packaged: 2019-01-05 19:19:48
Rating: Not Rated
Warnings: No Archive Warnings Apply
Chapters: 3
Words: 2,558
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/12196041
Author URL: https://archiveofourown.org/users/orphan_account/pseuds/orphan_account
Summary: When a Witch curses Dean, making him return to the age of three, Sam is in over his head. Lucky for him he meets a young woman who needs a place to stay and happens to be great with kids.  Sam agrees to let her stay, giving him more time to find a cure for Dean. But what happens when little Dean tries to play Matchmaker?





	1. Shopping

They made an odd couple.

The father was easily over six feet tall. In his arms he held a little three year old boy dressed in a grown man's T-shirt. His little bare feet were kicking and he was squirming in his Dad's arms. Trying to reach the display of baby toys while his poor, helpless father was struggling to hold onto his child and pick out some cloths for him at the same time.

I observed from my position across the isle in the midst of the woman's undergarments section. It wasn't until the little boy managed to lean far enough over the knock a row of little plastic rattles onto the floor that I lent a hand. I was just stepping out from the racks of woman's underthings when the man set his son down to begin picking up the rattlers. That was a mistake. Seizing this chance the little boy began running. Giggling happy and pumping his fat little legs, the little trouble maker was headed my way. Just before he reached me, though, he stepped on the hem of he way to big shirt and fell face first on the floor.

Acting quickly and purely on motherly instinct I swooped in and scooped him up in my arms. Bouncing him on my hip and moving quickly toward his Father. I knew from experience that I had about five seconds before he realized I wasn't his Dad and then he was really gonna throw a fit.

Making it to his father just as water works started, I passed the whimpering squirming child to his parental unit.

"There you go buddy, now you stay with your Daddy here and don't cause him no more trouble. He looks like he's had a rough day." I said to the little one as he tucked his face into his Daddy's shirt.

His tiny fists tightening in the material and holding it to his face, hiding from me.

I turned to his Dad. "Cute little guy you got there." I said. "My names Lily." I stuck out my hand.

He hesitated a second, then pulled his hand from his pocket and took my hand in his. "Sam." He said.

"Pleased to meet you." I firmly shook his head. There was a cool piece of metal cupped in the palm but I ignored it. probably keys or something. Still, it was a little odd.

"And who's this guy?" I asked, reaching out to ruffle the little boy's hair. He tucked his face farther into Sam's neck.

Sam bounced him on his hip. "This is Dean." He said.

"Nice to meet you too, Dean." I said. "Does your Daddy need a hand shopping, hmm? You causing him some trouble?"

Dean burrowed deeper into Sam's neck, his ears turning red. Sam bounced him on his hip. "You don't have to." he began but I cut him off.

"Oh it's no problem. I work with kids like him all the time. Beside, you look like you could use the help." Before he could resume the argument I set my purse in my cart and took the package of onesies from his limp fingers dropping it in with my new panties and bottles of shampoo. "There." I said. "What next?"

Sam stared at me for a second. Then shrugged. "I...I'm not really sure. Dean...there was a fire...his mom passed away and I..." He choked up, I could see the tears pooling in his hazel eyes and quickly stepped in. 

"I'm so sorry. Don't worry, I'll take care of the shopping for you. I've dealt with enough children to take care of this. You just worry about the boy for a minute. I've got this under control." I patted him on the shoulder and turned back to the rack of clothing. Now. It had been a few months since I last had a job at the daycare center, but I was confident I could manage a little shopping for a single man and his little boy. Who was adorable by the way.

I took me about thirty odd minutes of running around the store with the giant and his little angle in tow to have a cart full of just about everything they would need. In addition to my shampoo and panties and a package of razors.

Dean had begun to warm up to me by the time we got to the check out lane and was playing with Sam's hair as the cashier scanned out items. Sam tried to pay but I refused to let him.

"Its not a problem." I said. "You look like you could use a little help any way."

Sam stared at her for a long moment. "I...Thank you."

"Your welcome."

"But," Sam said shifting Dean on his hip and following me out of the doors into the parking lot. "I can't pay you back."

"Sure you can!" I said tossing a glance over my shoulder. "Let me crash at your place tonight. I'm just passing through town for a couple a days and would appreciate a real bed. No offense to motels, but my goodness their beds suck."

Sam snorted at that and pointed to a old black car parked not far away. "That's my ride."

I whistled. "Lordy. That's one beautiful car. You want this stuff in the trunk?"

He nodded, quickly opening the trunk. I elbowed him out of my way and swiftly loaded the bags into the space.

"There we go." I closed the trunk lid and brushed the dust off my hands. "All done. You guys have a great day!"

I turned to go, pushing the cart to a near-by line of them when Sam called me back.

"Wait!"

I turned to look back at him.

"Did you really want to spend the night? I...I could use some help with Dean. I mean, if you don't mind. I could-"

I cut him off before he could continue. "I don't mind. Could I ride with you though? My cars across town at the motel."

Sam opened the passenger door. "Of course."

Quickly returning the cart to its place and slipped into the car. The leather was soft and worn to the touch. Sam placed Dean between the two of us and turned the key in the ignition. The car purred to life.

"Sweet."


	2. Home Sweet Home

We pulled smoothly out of the parking lot and began moving out of town on some local two lane blacktop. The radio sang softly, some classic rock station humming the back ground as Dean giggled happily and pulled on Sam's shirt.

"So," I said. "Do you live around here then?"

Sam glanced at me, "Yeah. Just a little ways away." 

"That must be nice. Living in a small town."

"Yeah." Sam replied.

Dean had lost interest in his shirt and had begun to crawl into his lap. His little foot landed right between Sam legs. The car swerved slightly and Sam's eyes widened. I bit back a laugh and leaned over, lifting Dean smoothly off his Dad's lap.

"Here little man. Let's leave Daddy alone for a sec huh?"

Sticking out his lower lip into a pout, Dean tried to crawl off my lap. I held him back.

"No, Dean. Daddy's driving. We have to leave Daddy alone."

Dean plopped down in my lap, tears beginning to form in his eyes.

"We can watch him though!" I said cheerfully. "Can you see him Dean?"

He looked up at me, green eyes glistening. One chubby finger pointing towards Sam. "Daddy?"

"Yes Dean. That's Daddy." I said, covering his little eyes. "Where'd he go!"

Dean's little hands came up and he pried at my own, trying to move them. I let him, moving me hands so Sam popped back into view. Dean giggled.

"Daddy?" He said again, pointing to Sam.

"There he is! Oh no! He's gone again!" I covered his eyes again and the game was on. 

For the rest of the ride I would cover Dean's eyes. He would tug my hands off and giggle, pointing to Sam with an adorable, "Daddy!" It seemed like only a moment before we were pulling up to Sam's place.

It looked like something out of a book. The door itself looked like a box culvert with a brick filled arch in the center of which stood a metal door. Sam parked the car near by and stepped out of the door, coming around to take Dean from my arms. The little angle strained towards him, reaching up to his father.

"Daddy! Up!"

Stepping out of the car, I followed Sam through the door and down the steps into the house. The house itself was amazing. I followed Sam as he lead the way to the kitchen. We set the bags on the counter there while Sam grabbed a glass of water for each of us. I leaned against the counter, holding my glass in one hand and watch as Sam stood near the sink, trying to give Dean a drink while he tried to take the glass from him.

 

"No, Dean, let me hold it."

Dean didn't listen, pulling the glass and spilling the water down his shirt.

"Dean!"

Instantly Dean let go of the glass and his his face in Sam's neck.

"Dean, that's why you have to let me do it. Okay, bud?"

Dean nodded into his neck, sniffling loudly.

"Oh, don't cry Dean." Sam said, patting him awkwardly on the back.

I grinned, setting my glass down on the counter. "Here, let me take him."

Sam passed Dean to me and I bounced him on my hip. "Are you tired Dean? Do you need a nap? Hmm?"

Dean shook his head, yawning. "No, don't wanna nap."

I grinned. "Naptime. Where's his room?"

Sam cleared his throat. "Um..."

I bounced Dean again, he pulled on my hair. "Don't wanna nap." he repeated.

"Its down the hall here," Sam said, leading the way.

We walked through what appeared to be a library, past a room with a large map in the middle and started down a hallway lined with several rooms. A couple of the doors were open. I noticed a sword hanging on the wall of one of the ones we passed before we came to a door. Sam pushed it open to reveal a twin bed in one corner pushed up against the wall with a line of pillows between the edge and the floor.

Dean hid squirmed in my arms, reaching for Sam. "Daddy! Don't wanna nap, Daddy." He said.

Sam took him from my arms. "Your tired Dean." He said. "You need some sleep."

I turned down the covers so Sam could set Dean on the mattress. 

"Try to get some sleep Dean." I said. "I'll leave you with your Daddy." 

Sam shot me a desperate look while Dean clung to his shirt, still protesting that he didn't want a nap. I grinned and stepped put into the hallway. Standing just out of sight and listening carefully.

"Come on Dean. Nap time. The lady said you need to sleep so come on." Sam said, no doubt still trying to remove the child clinging form from his torso.

"No! Dean don't wanna nap!" Dean was still having none of it.

"Come on Dean. You need more sleep. Just take a nap. Please."

There was a moment of silence.

"Sing." Dean demanded.

"What?"

"Dean sweep. Daddy sing."

"You want me to sing to you?" Sam seems stunned.

"Daddy sing!" Dean repeated triumphantly.

"What should I sing?"

"Sing sweep song. " Dean ordered.

"Do what?"

"Sweepy song." Dean repeated impatiently. There was silence for a moment, then Dean began humming little snatched of a tune. "Sweepy song."

"Oh." Sam said softly. "Mom's song."

"Sweepy song!"

"Okay Dean." Sam took a breath and began.

"Hey Jude, don't make it sad."

I turned away, Sam's voice was heavy with emotion and i couldn't ease drop on this moment. I walked quietly down the hall, Sam's soft voice echoing in the empty space as i made my way back to the kitchen.


	3. A Quiet Evening In

**Notes for the Chapter:**

> Sorry its been so long. Here's a new chapter. :} Comments are very very welcome!! Hope you like it. I promise it won't be this long next time. Probably...

I waited for Sam in the kitchen, leaning against the sink with a glass of water in one hand and staring vacantly at the wall. He caught me by surprise when he rounded the corner. His eyes were red and glistening in the overhead light, and I could see the tear tracks on his cheeks. Wordlessly, I handed him a wash cloth and stood there silently as he washed the tell-tale signs of his tears from his face.

 

"Thanks." He said after a long moment of silence. "For helping. I...I wouldn't know what to do with out you. I just...Dean's..." He took a long shuddering breath. "I just don't know what to do half the time."

 

"Hey," I said, wrapping an arm around him and pulling him into a sideways hug. "It's alright. Just let it out. I know it's hard."

 

He took another shuddering breath hiding his face in his hands and he fought to control himself. Several minutes passed in silence. Sam wiped his face again, and stood there, still embracing him in silence. Sam was the first to move.

 

"I should put this stuff away." He said, stepping out of my embrace and moving towards the piles of grocery sacks on the floor.

 

Setting the glass down on the counter, I moved to help him. "I dunno where you want this stuff, but tell me what to do and I'll shlep."

 

"Shlep?" Sam repeated, lookup from where he was bent over the bags.

 

"My Mom used to say that." I explained, grabbing a bag of pull-ups and one of clothes. "Where do you want Dean's stuff? I can't put it in his room till he wakes up from his nap."

 

Sam nodded. "Yeah. Just put in his o-the room with the sword and stuff. I'll get them later."

 

"Cool." I said and started back to the hallway with the bedrooms. Sam's house was cool as all get out, but lordy it was gonna take some time to learn my way around.

 

It took Sam and I nearly twenty minutes to get the stuff sorted through and what we could put away. Afterwards we met in the kitchen again. I picked up my glass and filled it with cold water. Taking a sip I leaned against the counter.

 

"Here's to a job well done." I said.

 

Sam leaned over, clinking his glass with mine and taking a long sip. "So." He said after a moment. "Where you from?"

 

I snorted. "This sounds like a really bad blind date."

 

Sam ducked his head, a blush rising on his cheeks as he sheepishly rubbed the back of his neck. "I'm from Missouri."

 

"Kansas." He replied before hiding his still red face behind his glass.

 

An awkward silence filled the kitchen we both stood there, saying nothing and drinking water like two psychos.

 

"So." I said eventually. "What do you do?"

 

"What?"

 

"For a living. What do you do for a living." I clarified.

 

"Oh. Right." Sam cleared his throat. "I, uh, I'm in retail."

 

"Oh really?"

 

"Yeah. You know, move around a lot. Just all over the country really." He said.

 

"Cool."

 

"Yeah." He took a long sip of water. "How long did you say I should let Dean sleep?"


End file.
